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curated travel dates

Below are some destinations that either have a special place in my heart or are on my travel bucket list, so I have decided to offer them at these special discounted rates for extended bookings:

 

Overnight: $3500 (a $500 value)

One Fine Day: $4000 (a $1000 value)

The Weekender: $6000 (a $1500 value)

Each Additional Day:$2000 (a $2000+ value)

 

How It Works

Simply chose your desired destination and length of time. From there, we'll schedule a 30 minute phone consultation and design our perfect escape together choosing our hotel, restaurants and activities from the plentiful options listed. Of course I'm open to suggestions too! Upon deciding our itinerary, I will send over an invoice for my 50% deposit (minus the phone consultation fee), my airfare and our accommodations. Then comes the hard part...waiting for our amazing rendezvous!

Tried + True  Favorites

Image by Michael Discenza

New York City

​​The Big Apple! I've been so many times and yet still have so much to discover. Shall we put the moniker of "the city that never sleeps" to the test?

 

Hotels

Edition The Bowery Hotel The Ned Nomad  Mercer Gansevoort  The Chatwal Made Hotel Arlo Williamsburg Wythe Hotel Brooklyn

 

Restaurants

Avant Garden Tatiana Eleven Madison Park Aquavit Marea Per Se Celestine Olmsted 

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Activities

Live Jazz at The Village Vanguard Plays on Broadway Ballet at the NYC Ballet Day Trip to Governor's Island

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Museums + Galleries

MoMa The Met The Tenement  Museum The Frick Collection  Brooklyn Botanic Gardens

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Spas + Relaxation

Aire Ancient Baths Shibui Spa Great Jones Spa World Spa

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Special Events

NYC Fashion Week

Image by Antonio Cuellar
Image by Line Kjær
Mexico City

Mexico City

I visited Mexico City in May of 2024 for the first time and instantly fell in love! The food, the culture, the nightlife and (not so) secret speakeasies​...it's a magical place!

 

Hotels

Las Albacoas Marquis Reforma Casa Polanco The Wild Oscar  Brick Hotel La Valise

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Restaurants

Pujol Bakéa Carmela y Sal  Expendio de Maiz Sin Nombre Quintonil Sud 777 Máximo

 

Activities

Ride a Trajinera Through Xochimilco Attend a Lucha Libre Match Mezcal + Tequila Tasting at a Speakeasy Explore the Ruins of Teotihuacan 

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Museums + Galleries

National Museum of Anthropology Museo Jumex Museo Soumaya The Frida Kahlo Home + Museum National Museum of the Revolution

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Spas + Relaxation 

Aurora Spa​ Inspiración Spa Hela Spa En Dharma

​​​

Special Events

Pitchfork Music Festival Barra Mexico Dia de los Muertos

My Travel Bucket List

coming soon!

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Gem DeMilo is an independent, curvy, busty companion and proud owner of a certified super booty. Based in Chicago, she is also available for appointments in Evanston, Oak Park, O'Hare/Rosemont, Oak Brook, Schaumburg, Joliet, Aurora and Milwaukee Wisconsin. She also frequently tours New York City, Philadelphia, Boston, Charlotte, Atlanta, Florida and beyond! Gem is also available for bespoke travel anywhere for a FMTY. She is in her early 40s, making this redhead vixen both mature and youthful. Gem specializes in GFE with a focus on authentic connections and intimacy. She especially shines during cocktail dates, dinner dates and overnights. 

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